The Setauket Raid – December 1777

On the 1st of December 1777 Colonel Samuel B. Webb noted in his journal,[1]

… At Horseneck [Greenwich, CT]. This day my Regiment marched in to this place. An expedition is intended on Long Island…. We expect to cross tomorrow evening.

Sgt. Simon Giffin of Webb’s Regiment was a busy man that day. At North Castle (today’s Armonk, New York) he wrote in his diary, “turned out by gun fire this morning … Got the cartridges I went after and then set out for Rye.” Sergeant Giffin had been sent to gather cartridges for his company, Capt. Caleb Bull’s Company of Webb’s 9th Connecticut Regiment. Fortunately, he had been provided with a horse for the fifteen-mile ride through Westchester County to rejoin his regiment at Rye. There were Tory partisans operating in the area and he was carrying a heavy load, “enough cartridges to complete 50 rounds per man for 53 men,” a burden probably weighing some 125 pounds (less if some men already had some cartridges). Did he have a packhorse to carry his load? He doesn’t mention one.

Giffin’s diary, an unpublished manuscript in possession of the family, provides long-forgotten details about a time, place, and a host of fascinating characters, all neighbors, friends, patriots, soldiers, and writers. [2] He wrote in a personal form of shorthand that is challenging to read; the extracts that appear below are as much translation as transcription. During his seven years in the Continental Army he participated in some well-known campaigns, but his most revealing insights concern the many smaller actions that only marginally affected the course of the war, but that were every bit as dangerous and demanding as the major events. The Setauket raid is one of those stories.

By 3 p.m.on December 1 Sergeant Giffin was back in Rye only to discover that his regiment had marched off to Horseneck (today’s Greenwich, Connecticut) on the shores of Long Island Sound. He rode off again for the final six miles of his journey, rejoining the regiment at sunset, but his day was not over yet. As the evening shadows lengthened, he made a quick visit to the commissary, gathered three days provisions, and distributed them to the men with instructions to cook everything immediately, as the regiment would be on the road again in the morning. After his long day, Giffin found lodgings on the nearby farm of a Mr.” P. Somers.” Was he sleeping in the house or the barn, or a tent in the yard? He doesn’t say.

Sergeant Giffin spent the following day, December 2, in camp at Horseneck where he recorded that Privates Josiah Burris and Amos Porter were brought before a regimental formation for punishment. They had been convicted of desertion, a serious offense which usually resulted in a sentence of one hundred lashes or a hanging, but in this case Burris was set free and Porter was “picketed for 19 minutes,” a punishment that involved painfully balancing on one bare foot on a blunt peg, or picket.

The next morning, December 3, the regiment departed Horseneck, and marched east along the Connecticut shore through Stamford and on towards Norwalk. General Putnam had planned a three-pronged attack across Long Island Sound against three “lightly defended” British posts.[3] One wing of the attack under General Meigs would attack a Loyalist regiment at Jamaica. A second wing under General Parsons would assault British transports loading wood at “Hockaback” (modern Aquebogue) on Peconic Bay at the eastern end of Long Island. Colonel Webb’s raiders were ordered to attack a garrison of Loyalist troops at the village of Setauket on Long Island, near Stony Brook.

Several such raids on Long Island had occurred already that year, each resulting in skirmishing but none in decisive victory for either side. Now, in December 1777, General Washington’s spies in Setauket had informed him that the enemy garrison had been reduced in numbers and the depot at Setauket was bulging with supplies. Unfortunately, those same spies failed to notice that the British garrison had recently been reinforced with four swivel guns (light cannons). For this assault on Setauket, General Parsons dispatched a force of some 400 Continentals. Among them would be men from the 9th Connecticut Regiment; both Colonel Webb and Sergeant Giffin recorded details about the events.

According to Giffin, on December 4 Colonel Webb sent a scouting party of thirty or so men across Long Island Sound from Connecticut in whale boats to explore enemy positions around the Setauket Church. The next day he divided his main force into groups, assigning them to two sloops, the Mifflin and Spy, and the schooner Schuyler. Sergeant Giffin was assigned a squad of twelve men plus a corporal and ordered to board the privateer Spy tied up in the harbor at Norwalk, Connecticut. The raid across the Sound was to proceed as soon as possible, weather permitting, but the weather didn’t cooperate. Giffin described his week:

December 4, 1777 Clear and cold. We lay at Norwalk all day. There was a small ship that went over to Long Island with about 30 or 35 men as a scout in order to make discoveries. Nothing happened remarkable.

December 5: this morning orders came for all the Sergeants to parade before the Colonel; and I was ordered to take command of a guard of 12 men and a Corporal to go on board the Privateer that lay in the harbor at Norwalk.

We marched down as far as I could and haled the Spy, for the privateer was called by that name, but they could not hear us. I had to march back to my old quarter again. About sundown the boats came for us then I and the men with me went on board and we was divided into four watches with the men that belonged to the schooner. I was in the third watch. Nothing happened.

December 6: Severe cold weather. Lay in the harbor this day. The ice came down [the Norwalk River] by us rushing fast.

Cold weather, snow, and ice complicated the attack. On the evening of December 7 Captain Riglin of the Spy ordered his crew to “make sail” for Long Island. Giffin reported that the pilot, a local expert on sailing conditions in the area, “disappointed us.” Was he disappointed because the mission was scrubbed? Or, was it because the pilot gave up too easily? Whatever the explanation, the Spy returned to Norwalk harbor that night. The next day was cloudy and the Spy remained in the harbor all day and all night. In the morning Giffin walked into town to gather supplies for his men. He rested for the rest of the day and then “stood his watch” on the ship beginning at midnight. In his notes he reported that the wind was blowing hard all night.

The next day, December 9, the three ships remained in Norwalk harbor during the day, and then about 9 p.m. they sailed together out into Long Island Sound. The wind was blowing fresh from the northwest and the three ships soon parted ways. At 4 a.m. Captain Riglin of the Spy ordered his crew to “take in a double reef” (reduce sail to a minimum) and return to Connecticut. They made harbor and spent the night at Black Rock Point, near Bridgeport. Giffin reported that the three ships had been separated in the storm and it would be several days before he learned of the fate of the other raiding parties.

Foul weather on December 9 wreaked havoc on all three wings of General Parsons’ ambitious plan of attack. General Meigs’s raiding party departed Sawpits (Port Chester) in whale boats for the twelve mile trip across the sound to Hempstead Harbor. The whaleboats, each propelled by a single sail and sixteen oarsmen, floundered in the rough seas and gale force winds. They were forced back to Sawpits and the attack on Jamaica was cancelled. General Parsons’ fleet of small vessels bound for the eastern end of Long Island was slowed by the storm; by the time they reached Hockaback all but one of the enemy transports had sailed. Parsons’ men captured a coastal merchant ship and a dozen Tory volunteers gathering firewood for the British garrison in New York.

Giffin’s party of raiders on the Spy spent the 10th of December on shore at Bridgeport, where Private Burris deserted again “and went home to his family.” Later that day the Mifflin sailed into Bridgeport, reporting that on the night of December 9-10 she had successfully fought through the storm and landed her party of raiders near Setauket before returning. The next day the two vessels were ordered to sail up the coast of Connecticut to “Seamus Head” (not on modern maps), pick up more raiders, and then make a second attempt at landing men on Long Island.

Meanwhile at Smithtown Bay on the morning of December 10, General Parsons’ party of raiders from the Mifflin marched off towards the Setauket Meeting House, about four miles away. Their landing did not go unnoticed. Loyalist observers rushed off to Setauket to warn the British garrison of the impending attack. The Loyalist troops were manning the barricades as the Americans approached. For the next several hours the raiders blazed away at the enemy breastworks, the old Church, its stained glass windows, and steeple all lined with enemy marksmen. By noon they were beginning to run out of ammunition and General Parsons was forced to order a retreat. They would spend the rest of the week, December 11 thru 17, avoiding enemy patrols and waiting to be rescued.

According to Sergeant Giffin’s notes, General Parsons’ headquarters in Connecticut made several attempts to reestablish contact and to ferry reinforcements and supplies to Parsons’ men on Long Island. On Friday December 12, 1777, the Mifflin and the Spy again sailed out into the Sound, carrying reinforcements. At 3 a.m. Saturday morning the two vessels landed an additional 200 raiders at Smithtown Bay. This second wave moved inland towards Setauket but without Sergeant Giffin and his squad. They had been ordered to stay onboard the Spy as a security detail.

That afternoon, December 13, the two vessels returned to the coast of Connecticut, sailing past Old Saybrook and up the Connecticut River to East Haddam where they picked up more reinforcements from the local Colchester and East Haddam Regiment of Col. Henry Champion (the 3rd Connecticut Regiment). That evening the two ships returned to New London where they finally learned of the fate of Colonel Webb and the raiders on the schooner Schuyler.

On that stormy night of December 9-10, the Schuyler sailed alone, successfully fighting its way through the wind and waves. Then, at dawn as they approached Smithtown Bay, the Schuyler was confronted by a British warship, HMS Falcon. Colonel Webb later provided a report of his disastrous night to General Washington:[4]

On Tuesday evening December 9, I embarked on board the armed sloop Schuyler with 3 other vessels and about 400 men for Long Island. The night being dark and blustery we (our ships) parted company…. At dawn on Wednesday morning we [the Schuyler] were off Setauket when we discovered a ship crowding all sail for us, being to leeward we had only one chance to escape … grounding our ship on a beach about 200 yards from shore … The surf ran so amazingly high that She filled and sank … The enemy ship came within a half mile and was pouring in broadsides … in this cruel situation we were forced to strike. The British sloop of war Falcon brought us to Newport, Rhode Island …

Giffin’s notes reveal that his ship, the Spy, made several more attempts that week to return to Long Island to pick up survivors. It would be the 17th of December, however, before they made contact with Parsons and were able to evacuate the scattered remnants of his raiders.

Sabbath December 14, 1777 [we] sailed from New London in order to go to Long Island but the wind blew hard and a heavy sea going and we were obliged to put back again to New London … [Later] we were called up to sail for Long Island about 3 o’clock at night.

Monday December 15, 1777 we sailed for Long Island the wind blowing fresh. We came to anchor at Oyster Pond [Bay?] where we sent an express to General Parsons to see whether we were to wait for the troops or not as they were not here.

Tuesday December 16, 1777 we lay in Oyster Pond harbor waiting for the troops but they did not come as we expected to have them. Nothing more remarkable happened.

Wednesday December 17, 1777 this morning some of the troops came down and embarked on board the vessels that lay waiting. And, got the General on board and set sail for the lee breezes were brisk about 12 o’clock in the fore [noon]. [We] landed all the men and lay at Saybrook all the remainder of the day until night. It rained all night.

Webb’s raid on Setauket was a disaster for the army and for the Connecticut River communities around Wethersfield, home to the men of Colonel Webb’s Regiment. Among those captured were Colonel Webb, army Capt. Edward Bulkley, sea captain John Riley of the Schuyler, and some sixty-five enlisted men. Their families must have been devastated by the loss at one time of so many local men.

Following the calamity on Long Island, the balance of Webb’s Regiment gathered at New London, Connecticut. On December 22 they received orders to return home for winter leave. It would be their first visit with their families in seven months. They were among the fortunate ones who would be spending a month at home rather than with the Grand Army at Valley Forge.

[2] Simon Giffin, The Diary of Quartermaster Sergeant Simon Giffin of Col. Samuel B. Webb’s Regiment 1777-1779. See Also: Record Book of Quartermaster Sergeant Simon Giffin 1779-1783. Photocopies and microfilm of the originals are available at the Connecticut State Library and Archives in Hartford (CSLA). Originals are with the family. Special thanks to Robert E. Mosier jr. for providing the author with an original photocopy for transcription.

Zak: Thanks for your note. You may well be correct. Generals Putnam and Parsons both mention Huntington LI near Oyster Bay (Ref: Hall. “Life of Parsons” p. 108) thus I assumed that might be the rendezvous point. However Tory newspapers reported that the survivors moved east towards Montauk Point where there is another Oyster Pond as you suggest. Living in Wyoming I spend a lot of time with old town histories and maps as you can imagine. My guess is that your Oyster Pond on Montauk Point is a more likely evacuation route, you are probably correct. Thank you, Phil

As a resident of Orient Long Island, I have a voracious appetite for our rich Revolutionary War history. I commend Mr. Giffen on his excellent piece! Even though Montauk does have a place called Oysterponds, I think it is more likely that the Oysterponds referenced in Sgt. Giffen’s journal is actually what’s known as Orient Harbor today. The Montauk Oysterponds is really just a pond, not open to the ocean. By contrast, Orient Harbor is a protected anchorage with easy access to Long Island Sound, and is directly across from Saybrook Connecticut, where the expedition ended. Also a march from Setauket to Orient would keep the soldiers along the north shore of the island and within sight of rescuer’s sail, while a march to Montauk would be many more miles for unsupported troops that were low on supplies. I am going to follow up with the Orient Historical Society to see if I can find out more. Possibly your relative’s record is the only documentation of one of the many daring raids conducted in these parts so long ago.

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Journal of the American Revolution is the leading source of knowledge about the American Revolution and Founding. Appealing to scholars and enthusiasts alike, we feature meticulous, groundbreaking research and well-written narratives from scores of expert writers. Our work has been featured by the New York Times, TIME Magazine, History Channel, Discovery Channel, Smithsonian, Mental Floss, Mount Vernon, and more. Journal of the American Revolution also produces annual hardcover volumes and its own book series.